Fated to Pretend
by Anti-canon
Summary: As a child Stiles used to play dress-up with his mom, and now that she's gone he does it to feel more himself, feel closer to her. It doesn't hurt when gorgeous men in sleazy clubs take notice either. Basically an excuse for me to write crossdressing!Stiles. :P
1. Feeling Rough and Raw

**A/N: If you've read any of my SPN stuff then you'll know I have a whole 'verse completely devoted to crossdressing because I just love it so very, very much. When I discovered that I hadn't written it for Teen Wolf yet, I freaked out and started brainstorming like crazy because I need to see all those boys in some quality lingerie. :P There may or may not be appearances from everyone else. Haven't decided yet. Though the appeal of and Isaac in fishnets and corsets is quite overwhelming.**

**Anyways! I don't know where this is going or what's gonna come of it, but if you want to come along for the ride, that would be grand. ^^ Title stolen from MGMT's Time to Pretend. which I used to kinda set the tone for this piece. Please lemme know what you think!**

_Stiles_

You always put the rouge on first- painting just the outline of your lips with a kind of reverence very few show the process these days.

It's counter-intuitive, you know, but it's how everything started and without the ceremony of it all, you wouldn't be here, wouldn't feel the need for it, wouldn't still be holding on to her. So you perch yourself in front of her old vanity, white paint cracking and peeling, water spots ever present on the old glass mirror, and pull out a bag of wipes, cleaning down every inch of your face before starting in.

Stripping down completely, you are utterly bare in this moment- raw, straddling the knife's edge. From the chest up, without the obvious exception of course, you are nearly androgynous, and you find an odd sense of comfort in it. You could be whatever, whoever you want to be. Right now, you're done with the sheriff's son, tired of the overactive boy who never knows what he wants or when he's wanted. It's time to tuck him away, to let him rest and become someone else entirely.

The deep mauve surrounding your lips turns the pink tissue lush and full, making your face more feminine, makes your pointed features stand sharply out. A thin line of ink black eyeliner, liquid and intense, changes the playful, mischievous brown eyes to something sharper, darker. A dusting of dusky orange eyeshadow sets them aglow- makes them alive and searching, draws attention away from the thick eyebrows. The lightest of blushes with just a smattering of glitter makes your cheekbones delicate, makes the upturn of your nose devilish.

With the cut of your hair you're already the perfect pixie and you can feel these other parts of yourself start to bleed back through, to envelop that blank canvas of before. When you stand and turn, strut to your room, your walk is more confident. There's a sway to your hips, and attitude in the swing of your arms, a purposefulness as you step on the balls of your feet. There's a false bottom in your wardrobe- easily lifted with a spare screwdriver- and in the empty space carefully folded clothes sit, waiting.

You consider black satin for tonight- comfortable, classic, but it's the red lace panties that make the cut. It's a bit of a tight fit, not having been designed with your equipment in mind, but you get situated comfortably enough. You find skirts are best left simple- something with ruffles, to grab attention, but it's the skin that you want to steal the show- legs are the most underrated lure. You don't shave them, your mother was always complaining about how much she hated it, and you never saw the need. If men were going to be scared off by your gender, better it's the hairy legs they find off putting than a growing erection.

You almost go with a floral top, but decide against it. Floral is flirty, floral is asking for your number and biting your lip and a hug with a pat on the back. You want free drinks. You want hands trailing the back of your thigh. You want rutting in the back of the cab and sneaking out of an apartment in the middle of the night. You want something obvious, something… masculine and therefor obvious. You want a tight white v-neck and a black vest, so you abandon the women's clothing and take some from your closet instead. Diversity yields the best results after all.

Jewelry is more hassle than it's worth come morning and high tops are the only way to go. You couldn't walk gracefully in heels no matter how badly you wanted to, and anyway you never did find an appeal in shoes, even if you had a love for all the other pieces of an ensemble. Besides, you don't need the added height. The kind of men that want drunken escapades in a bar aren't all that interested in people taller than them, no matter you're playing at an interesting sort of game. Fake ID, money, phone are all tucked in an inside pocket in your vest, and the next time you pass the mirror on the way out, you aren't you. At least not the version from before. Right now you're Genim, not Stiles, and you're closer to her than ever.

* * *

_Derek_

He's just stepped off the dance floor, legs trembling just the smallest bit from exertion, sweat glistening off his brow, and easy smile hanging off those unbelievably full lips.  
You've been watching the whole night, eyes glued to his frame from the moment he came through the doorway. There's something about him, it's hard to explain, but it draws you towards him like a moth to the flame. He's so open, so unafraid, unable to be anything but himself. When you catch his eyes it makes your breath stutter, your stomach drop, your jeans tighten.

You've been warding off every man, woman, boy, and girl that's come up to you throughout the night, not interested in anyone's company but his. And yet, it seems as though he's the only person in this whole club who hasn't tried to approach you yet. You've seen the way he's scanning the crowds, know that he's looking for something to quell the loneliness, but he's been flighty, quite particular the whole night.

He is, without a single ounce of shame, a complete and utter cocktease, and he knows it. You've noticed those smirks, the sparkle in his eyes, the flush of his cheeks and ears when he gets a man going, makes him really hot and bothered, and then just drops all interest. He's done it to a fair handful already- gotten himself several drinks pushed into his hands, numbers tucked into his skirt, knees pressed in the v of his legs, but he's not chosen anyone just yet.

You swear he's made a few guys shoot their load- touching and grinding and stealing their breath until they quake, close their eyes, groan, and walk away. He's a vixen, a big fish in a little pond, and he's waiting for his equal. Making a decision, succumbing to this gravity, you put down your drink, break through the small crowd surrounding you, and stalk over to him.

Boys like him, these manipulators, are usually only playing the predator, more interested in catching the attention of the top of the food chain than exerting any real power of their own. You're certain you've got him pinned, know just how to make him weak, make him fold beneath you. Coming up behind him, you skirt a hand around his naked thigh, cage him up against the bar, breathe hotly down his neck. "You ought to be more careful with yourself, could drive a man mad with this act."

He turns his head, blinks slow and calculated, licks his lips, and damn if he isn't one big fish. He spreads his legs beneath your touch, arches up into you, keeps his gaze half-lidded. "If you can still speak, I'm clearly not being careless _enough_." He leans in, just slightly, and rakes his teeth down your chin. Your mouth goes dry in an instant and your hand drops off his leg, coming up to touch at the burning lines he just made. "You ought not underestimate me."

With your attention decidedly elsewhere he maneuvers out from under you, puts an extra sway in his step, and makes a bee line for the exit, not bothering to glance back as he disappears outside.


	2. Love Must be Forgotten

**A/N: Oh god... Someone please stop me. Like really. I need someone to come on over and shake me good and hard and tell me that I've got to get my brain sorted out.**

**Basically this chapter is an excuse to dress up some more of the boys. :P I actually came across a site (enter shameless mode... now) while drifting around a few porn blogs that is just dedicated to men in skimpy underwear and stockings and stuff and that good stuff and it's AMAZING. Anway! There's no chance in hell y'all wanted to hear that, but I swear there's a point to it- I have piiiictures :D You'll have to grab the link from the AO3 version since they don't allow thinks here, but you definitely should. ^^ Muy NSFW, but soooo worth it. :P**

**Beware- unbeta'd as per usual. Also, I have no idea where I'm going with this. :P In any case, love to hear what you guys think!**

* * *

_Derek _

You'd never thought you'd see him again.

After you'd gained your senses, run out into the alleyway behind the club and found it empty, you were certain he'd always be "the one that got away." Of all the places in this city, you couldn't have possibly imagined that you'd run into him here. That night there was something about him, this otherworldly sort of aura. He hadn't seemed real, instead some kind of fever dream- sprung to life by the collective desire and lust and longing of all the lonely hearts in the bar. You'd been content to believe this, to think of him as a specter, a haunting of his body and mind. It was far more appealing than the alternative- him being a real entity, a unattainable perfection you'd let slip carelessly through your fingers.

Instead, you're thrown into the harsh reality of it, standing just thirty feet away in a dingy supermarket. It's something like two am and the appeal of a late night junk food binge had drawn you down from your apartment, here. If you were a different person, you might call that fate. As you are, you see it as an opportunity- a cosmic gift given to you on the pretense that you act or lose luck's favor forever. He's in a group this time, a boy like him flanking each side. Well, there's not really any boys _like him_, but still.

One's got dirty blonde hair, all gathered up in neat curls on the top of his head. He's dressed something like a schoolgirl, all greys and blues and whites. He's got a modest skirt and knee-high socks, a vest and button-down blouse, a pair of flats and a skinny tie with just a dash of blush to color his cheeks. Innocent and shy, just a step up from 'plain', he's a pervert's wet dream, but he doesn't seem to notice.

The other boy, he's beautiful in the way that makes a person nervous, that kind of perfect that sets you on edge. His features are smooth but firm and his make-up is immaculate- lips and eyeshadow glimmering a fiery gold. The army green half-jacket clinging to his shoulders is probably more expensive than your rent as are the black boots zipped all the way up to his knees. There's a teasing stretch of skin before the hem of his skin-tight mini skirt, black leather, and there's most definitely no panty-line in sight.

Then, there's _him, _unconsciously putting them both to shame. His eyes are smoky, his lips are luscious, his sway could hold a thousand eyes. A simple, black minidress hugs his hips and his ass, the plunging neck line accenting his clavicles, the hemline just short enough to reveal the crotch less cut of his fishnet stockings. The oval, white fringe starts mid-thigh and swoops gracefully up into the dress, making your mouth dry and your heart race, wondering if a peek beneath would reveal skimpy underthings or just ripe, wetting manhood.

You're gathering yourself to go over there and talk to him, ruffling your hair, pulling the waist band of your sweatpants down so just the hint of pubes stick out, losing the tattered flip flops- far better to be barefoot- when he catches you looking. Recognition flashes instantly, but the Cheshire smile that spreads across his lips comes slow as molasses. The boys next to him notice the shift in attention and follow his gaze. When they see you, they draw closer, Wet Dream placing possessive hands on his thigh and shoulder while Upper Crust pulls a leg between his own, pressing up against his side like a cat in heat.

Instead of putting you off- which is clearly the intention- you grin, all teeth, pleased that you're seen as a threat. You abandon your grocery cart, stalking over and stretching your arms above your head, letting your t-shirt ride up and your sweats slip lower. The move is beyond obvious, but it makes _him _lick his lips appreciatively. "Why, if it isn't the big fish in the little pond…" You make it clear that you think he's yours for the taking, completely ignoring the other two and running the back of a finger along that bare patch of skin between his thighs, venturing up into the dress when he doesn't make you stop.

"And the mangy mutt who thinks himself a wolf-" He gives you a long, lingering once-over before stepping forward in a rush, making your hand come straight up to fondle him through a thin layer of fabric. The brashness of it catches you off guard and makes you shudder, breathing hitching when he bites his bottom lip and _moans. _"I'd love nothing more to stay and play with you a while, but I'm on a bit of a schedule." Without breaking eye contact, he motions his friends closer, and the three of them close in around you. Hands disappear up your shirt and beneath your pants, groping your ass, pinching your nipples, cradling your cock, and then he's right up in front of you, eyes hooded, lips centimeters from your own. You can feel all three of them breathe hotly against your skin and already you're hard and dripping, muscles thrumming like a live wire. His tongue darts out to lick at the seam of your lips, you close your eyes, and in a rush, they're all gone.

You open your eyes to see them sauntering away, not a single one throwing a backwards glance, while you stand in the middle of the produce section, ass crack bared to the wind, pants tent-poling and damp, jaw hanging nearly off its hinge.

* * *

_Stiles_

Issac and Jackson only think to question you why the hell you just had them molest a stranger in the middle of the grocery store _after _the three of you are curled around each other, sweaty, breathless, and covered in spunk.

You can't help but laugh at their clear sense of priority, but give in when they give tag-team puppy eyes. It's their forte, though double penetration comes as a pretty close second. "He's just some guy I like, and by like I mean torture." You shrug as though it's not much deeper than that, as though the very sight of him doesn't make you ache in places you didn't know you had. To them you're just that slutty club boy they invite to their bed, spicing up the couple routine. Sure, your friends enough, but not nearly close enough to share emotional crises with. You're here because you're fun, you're careless, and so that they can have sex and both top. The parameters of your acquaintance are unsaid, but clear all the same.

So you give them both a lazy smile and a wet kiss, humming pleasantly when Isaac plays with your soft dick and Jackson scissors your dripping opening, the both of them pressing rousing erections against your hips. You moan and sigh and scream at all the right times. You make sure neither one gets more attention than the other and make sure they kiss each other and not you when they come.

With the complexity of it all you most certainly don't have wits to think about Tall, Dark, and Bad Touch. Nope. Not at all. Not the seafoam green of his eyes that you've never seen before in your entire life. Not the predatory, shit-eating grin, or the slight buckteeth that make it just a hair less intimidating. Not the chisel of his sharp jaw and the grizzled, sexy, sultry, fucking _sinful _covering of stubble or the ridiculously slim waist and broad chest and firm ass and perky nipples and- Er…

So maybe you thought of him a little. And maybe, sometimes, occasionally, when you closed your eyes, you imagined him surrounding you, him whispering against your skin, him stretching you out and filling you up and hammering you open. Maybe, just maybe you were walking out of that market just as turned on as he was and maybe you came while thinking about the filthy ways you touched him.

Maybe, possibly, there's just the slimmest chance you're screwed. And not even in the fun way.


	3. Everything Must Run Its Course

**A/N: Heyyy! I finally updated! :D This one's a bit of a change of pace, but I felt like I was missing some of the tenderness that was in the first chapter, so I reeled back a little. :P But you can be assured there will be plenty of shenanigans come next chapter. ^^ **

* * *

_Derek _

You knew that you were going to see him again.

Unlike that first time, you were sure of it now. There was some kind of inevitability about the whole situation that rid every ounce of doubt, that made you think, just maybe, just this once, there could be larger forces at work. Sure enough, once you set your mind to it, once you accepted that it would all happen so long as you stayed confident, it only took a week to find him in the crowd. You still feel that nervous thrill when you spot him, wanting to be shy and skittish for just a moment before you remember the terms of this little game you've been playing, the tentative intricacy of the back and forth when something is new and scary and wonderful.

This time is different though, this time the tables are turned, because you don't see him as you have before. This time he's the one caught off guard, the one stumbling into your territory. Spastically coaching an older man struggling on a treadmill, he is devoid of his form-fitting clothes, his fierce make-up, his focused confidence. Standing in the middle of the local gym, he's just a lanky boy, awkward and forgettable, not the viper-like vixen from before.

He knows immediately when he's been spotted, you can see the way his eyes widen as his mouth falls open into a comical "o". Finally feeling like the predator you were previously trying to be, you step off your own machine, grabbing the small towel hanging off the side to wipe some sweat from the back of your neck, and stalk over, a cocky grin breaking loose. The older man takes notice that the boy beside him has fallen silent for the first time in the past fifteen minutes, and stares over at him, concern clear before he follows the gaze and comes to glare at you.

He stops the treadmill immediately, stepping off and cutting in front of your target, eyes steely and jaw firmly clenched. "Can I help you with something?" A protective arm reaches behind him and clutches at the boy.

You have to force yourself to look at him, to pay attention to anything besides how beautiful _he _still is, even without the get-up. "I'm just a friend of uh…. ah-" You gesture behind him, feeling the back of your ears heat when you realize that you just put yourself in a very awkward place.

"Dad! Cut it out. He just wants to talk to me." He has to struggle a little before he pushes his way out from behind the man's back and he smiles nervously, fidgeting below both of your gazes. "Take a lap, get a drink, just-" He throws his arms up and nods his head in the direction of the locker rooms, trying to be subtle about his shooing gestures and failing miserably.

His dad glances back and forth between you and him, clearly skeptical, but leaving anyway, after shooting daggers at you in warning. "It's Stiles by the way. For future reference. I mean- not that there's gonna be a future necessarily, I just… thought you should… know." Stiles nods his head several times, swallowing thickly while avoiding any kind of eye contact.

"Stiles…" You can't keep yourself from smiling, pleased to finally have a name to put to the face, not admitting that you'd spent hours pondering over it. "It suits you- different, weird, good." You can tell that he's more vulnerable here, like this, but instead of activating that killer instinct like you thought it would, instead of thinking that you're finally going to snare him, you reel back, feel a strange protectiveness bleed through. "I'm Derek, just so _you _know." You nudge him lightly with your shoulder, try and get him to look at you, to let him know that you're not going to bite. As much as you'd been excited to continue on with this game of chicken you've been playing, as much as you still want to rush him into one of the bathroom stalls and make him _beg _for you, mark him up and tear him down and leave him quivering and raw, you're finding it all too easy to drop it all in the wake of his discomfort.

He's not the boy from before, you can tell- and not just in appearance, though the way he's holding himself, the way he moves and interacts is a give-away. He doesn't have that confidence from before, the playfulness, the surety of himself. When you just laugh softly, bump him again and press your smile to his temple, he whirls around, expression shocked and pleased. "I-uh… What're… I-" All he can manage is a fluttering smile, but there's so much appreciation and gratitude there that you don't mind so much.

"I'd better let you get back- your dad looks like he's going to self-combust if we make him wait much longer." You bite your lower lip and let a little of the old heat come back into your eyes, touching the inside of one of his wrists teasingly. "I'll be at The Red Door on Friday though. You should come find me." This time, you're the one who walks away, and even though it's killing you not to be able to glance back and gauge his reaction, you make sure to keep your head turned resolutely forward.


	4. Our Decision to Live Fast

**A/N: I... Uh... Ya. This is... a chapter. And almost nothing happens. I'm sorry. Mostly. All I can really say is that the next two should make up for it? We'll hope. Let's also hope they stop getting progressively shorter.**

* * *

_Derek _

You're not sure what exactly what you were expecting— Well, that's a lie.

You'd run nearly every possible scenario through your head over the course of the week, and good or bad, at the very least you felt as though you were prepared. If he came in, the nervous boy from before, you'd whisk him away to a quieter, calmer corner. You'd ply him with a few drinks, get him talking, buy him nachos. A little lacking in the heat from before, a little nicer than you're comfortable with, well aware that every minute you're warring against your inner asshole, but probably just what he'd need. Somehow, in your head, that ends with you becoming his big gay mentor, having to watch as he eventually comes out of his shell, falls in love with a douche name Brody, gets his heart broken, and you're left trying to pick up the pieces… It's nice, in a way, but not—just no.

But if he came in like before, armed to the teeth, harem of boy wonders hanging around his shoulders. You'd still buy him a drink, but then it'd be out to the dance floor, to finally have your turn of feeling him up and turning him around, making him dizzy with it. Odds are, you'd fuck him in a bathroom stall, clothes on, dirty and quick. You'd exchange numbers afterwards, but you can't help but feel as though that's the easy path to a fuckbuddy friendship. He'd call you up whenever he's drunk or lonely and you'd show up every time, hoping this time would be different, but all you'd ever do is have sex so good it short circuits your brain, and then he'd ask you to clean up and leave before he falls asleep. Just the idea of it leaves a bitter taste in your mouth.

You've tried not consider that he might not show up at all.

You're there for an hour, an absolutely excruciating hour of glaring at any person who even thinks of making a pass, gripping your glass so tightly it might just shatter, head snapping to the door every time it swings open. You swear to god you're going to get an ulcer from it, and you're beginning to seriously doubt everything about yourself, from your looks to your charm to your intelligence when he skitters in. You don't really recognize him at first, not right away, but then he smiles softly when he catches your eyes and waves jerkily.

As he makes his way over, you get a little short of breath and throw back the rest of your drink. He's not doing anything you'd expected. A strange amalgamation of all the versions of himself you'd seen before, he's got on a pair of black peep-toe shoes, the wedge heel just an inch and a half, and a bright white peeking from the cut-out. He's wearing a ribbed pair of cream-colored thigh highs, three pale blue stripes at the top to match his ruffled skirt. It clings to the sharp jut of his hips, giving just the barest tease of soft skin and dark hair before the hem of his white tank top. Covering his shoulders is a semi-sheer peach jacket, draping down past his waist in soft folds. And to top it all off, his lips are a soft matte pink, mascara and eye liner make his bright eyes pop, and his unruly locks have been pulled back into a wavy do with small pastel peach barrettes.

He's undeniably pretty and sexy and yet still a little shy and awkward. It's making your mouth dry and your chest tight. You know that you're staring when he ducks his head and blushes, but you just can't bring yourself to care. You wipe your hands on your jeans several times, and try not to notice that you can hear the pulse of your heartbeat over the thump of the music. When he finally sidles up to the bar, next to you, he lets the tips of his fingers skim across your arm before resting on the top of your palm, light, but purposeful. "Hey." There's a glimmer in his eyes that belies the nervous twitching of his mouth and you have to take a deep shuddering breath before replying. Attempting to pull yourself together, you lean into him and press your lips to his ear, using the thundering bass as an excuse.

"You are incorrigible, you know that?" You tongue, ever so lightly, at the shell of his ear before pulling back, and can't help but grin when you see that his pupils have dilated. He smirks at you and tugs at his bottom lip with his teeth, fluttering his eyelashes in a way that should be obvious and terribly calculated, but still gets your nerves thrumming.

"And what're you gonna do about it… big boy?" He moves his hands to come up and grip at the lapels of your leather jacket, coquette, but sincere. You know, with just that one move, that the two of you are not spending your night here. It's not anything you anticipated, but it's so, so much better.


End file.
